When Learning Feels Hard (and What to Do About It)

If you’re in software, you’re in the business of constant learning. Languages evolve. Tooling shifts. Frameworks multiply. Staying relevant is part of the job.

Many of us carry this need to stay relevant as a low-grade fear: What if I fall behind? That anxiety can quietly turn learning into a chore—or worse, something we avoid altogether. Ironically, that feeling makes it even harder to get motivated to catch up.

I found that the best way to break this cycle was through low-stakes projects I could play with. My GitHub history is littered with whimsical throwaway repos, sometimes built just for a joke. But I treated them seriously: using current libraries, trying new language features, applying real-world methodologies. These were my playgrounds—a safe space to explore, learn, and grow.

This playful approach did more than make learning enjoyable. It helped me bypass fear by tapping into curiosity and novelty. And more importantly, the learning stuck.

What the Research Says About Joyful Learning

This isn’t just personal experience. Research strongly supports the value of joyful, self-directed learning. When we approach something with curiosity and autonomy, our brains become more open, flexible, and primed for growth.

Here’s what the science says:

• Autonomy fuels learning. Choosing what and how to learn boosts performance—especially on complex tasks. A meta-analysis by Patall et al. found that offering learners choice significantly increased both motivation and results.
• Curiosity primes the brain. A study by Gruber et al. showed that curiosity lights up the brain’s reward system and memory centers, helping us retain both the target material and incidental facts.
• Joy broadens thinking. Barbara Fredrickson’s broaden-and-build theory found that positive emotions expand our thinking, boost creativity, and improve problem-solving—the ideal mindset for technical work.

When learning feels like play, we retain more, explore more, and grow faster.

My Career, Powered by Play

Over the years, I’ve spun up countless side projects. Some were practical. Most were delightfully silly. None were mandatory. But every one of them taught me something.

I built Slack integrations to test new frameworks, which turned into hands-on learning in CI/CD pipelines and deployment workflows. That work sparked an interest in open source collaboration and helped me build friendships with people across the world. I learned a ton about async workflows and effective communication—and those lessons still shape how I lead teams today.

Eventually, I built so many Slack integrations that I created a testing harness to streamline the process. That caught the attention of Slack’s developer advocacy team, opening doors in my career I hadn’t even considered.

And to think, all of this started because I wanted to post cat facts in a Slack channel. Looking back, the pattern is clear: play leads to learning, and learning compounds.

Every Project Has Two Outcomes

One mindset that’s helped me get more out of every project is to consider dual outcomes:

1. The project outcome: You build the thing. Maybe it works, maybe it doesn’t.
2. The learning outcome: You pick up a new skill, workflow, or mental model.

The second outcome is the one that multiplies. It shapes all future success, regardless of whether the original project succeeded.

And once I started valuing the learning outcome more, I felt less pressure about getting the project outcome “right.” That freedom led to more creativity. Ironically, by focusing more on what I could learn over the project outcome, I ended up with better results!

A Simple Framework: Play → Learn → Apply

This mindset is easy to repeat:

• Play: Follow your curiosity. Choose something that looks fun or interesting.
• Learn: Tinker, explore, and experiment. Let questions guide you.
• Apply: Bring what you learn into your work, team, or next idea.

You don’t need hours. Even 20 minutes of focused play can unlock something valuable.

Applying the Mindset to Yourself

While side projects are the ultimate playground, you can make this work for you right the middle of your workday, especially when you’re stuck or facing something unfamiliar. This isn’t a license to go wildly against conventions of your team or blow past deadlines, but working within the constraints you have there is still a lot of room to experiment and learn.

Instead of freezing up, ask:

• What can I play with? Is there a tool, approach, or idea I’ve been meaning to try? Could I reframe working with an existing tool as a way to play with it and explore it’s capabilities?
• What could I do differently? Could I build a quick prototype? Explore an alternate pattern?
• How can I make this more fun? Could I frame it as a mini challenge or “what if” experiment?

This playful mindset turns blockers into launchpads. It helps you learn faster—without fear of failure.

Applying the Mindset to Your Team

As a manager, I’ve found that modeling this mindset and creating space for curiosity does more for growth than any formal learning plan.

Give your team room to explore. Let them choose how and what they want to learn. That recipe of autonomy plus curiosity fosters intrinsic motivation and deepens learning and retention.

Consider adding playful learning into your team rhythms:

• Try a quarterly “Play Day” where people tinker with something new, then share it in a short demo.
• Give space in retros or planning to ask: “What are you curious about right now?”
• Celebrate small, joyful learning wins alongside project milestones.

These practices don’t just teach skills. They build confidence, creativity, and momentum.

Your Career Is a Playground

Your career is too important to be joyless. Play isn’t a distraction from progress—it’s one of the best ways to make progress. It keeps you curious, nimble, and open to what’s next.

So the next time you feel stuck or overwhelmed, don’t default to grinding harder. Pause. Look for the spark of curiosity.

Then play. Learn. Apply. And repeat.

Photo by Fallon Michael on Unsplash